Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (5): 1974-1981.DOI: 10.6023/cjoc202101038 Previous Articles     Next Articles

ARTICLES

基于亲电氯代反应的次氯酸荧光探针构建及细胞成像研究

赵云1,*(), 李艳芳1, 李蓉晓1, 王雅卿1, 樊晓霞1   

  1. 1 太原师范学院 山西晋中 030619
  • 收稿日期:2021-01-22 修回日期:2021-03-15 发布日期:2021-04-06
  • 通讯作者: 赵云
  • 基金资助:
    国家自然科学基金(21807077); 山西省自然科学青年基金(201801D221081); 山西省高等学校科技创新(201802100)

A New Fluorescent Probe for Hypochlorous Acid Based on Chlorinium Ions Recognition Mechanism and Its Bioimaging Research in Living Cells

Yun Zhao1,*(), Yanfang Li1, Rongxiao Li1, Yaqing Wang1, Xiaoxia Fan1   

  1. 1 Department of Chemistry, Taiyuan Normal University, Jinzhong, Shanxi 030619
  • Received:2021-01-22 Revised:2021-03-15 Published:2021-04-06
  • Contact: Yun Zhao
  • About author:
    * Corresponding author. E-mail:
  • Supported by:
    National Natural Science Foundation of China(21807077); Shanxi Provincial Natural Science Foundation for Youths(201801D221081); Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi Province(201802100)

A simple phenothiazine-indanone conjugated fluorescent probe PIOCl for HOCl was designed and synthesized. For the first time, a new fluorescent probe for HOCl based on Cl+ induced the unique electrophilic substitution reaction under the physiological conditions. The probe PIOCl was a turn-on response to HOCl, and the fluorescence intensity increased more than 600 times after addition of HOCl. In the range of HOCl concentration from 0 to 6.0 μmol/L, the fluorescence intensity had a good linear relationship with HOCl concentration ( R2=0.997), the detection limit was 1.40 nmol/L, and the naked eye detection as low as 0.25 μmol/L and rapid response (<3 s) can be achieved under 1.0 μmol/L HOCl. The sensing mechanism of probe PIOCl for HOCl was verified by NMR, HRMS and density function theory calculations. Using fluorescence imaging technology, the endogenous and exogenous HOCl has been successfully detected, which indicates that probe PIOCl has potential application prospects in analytical detection and pathological analysis.

Key words: hypochlorous acid, fluorescent probe, electrophilic chlorination, indanone, turn-on mechanism